US8299201B2ExpiredUtilityPatentIndex 61
Bismuth-catalyzed polyurethane composition
Est. expiryOct 8, 2022(expired)· nominal 20-yr term from priority
C09D 175/04B01J 31/1805C08G 2190/00C08G 18/4866C08G 18/227C08G 18/12
61
PatentIndex Score
2
Cited by
10
References
19
Claims
Abstract
A one-component polyurethane composition includes at least one polyurethane prepolymer having terminal isocyanate groups which is prepared from at least one polyisocyanate and at least one polyol, and to at least one catalyst system which is obtainable from at least one bismuth compound and at least one aromatic nitrogen compound. The polyurethane composition may be used as an adhesive, sealant, coating or lining. Finally, catalysts for polyurethane compositions are disclosed which represent coordination compounds between bismuth and at least one aromatic nitrogen compound.
Claims
exact text as granted — not AI-modified1. A one-part polyurethane prepolymer composition comprising, in a single part,
at least one polyurethane prepolymer having terminal isocyanate groups, prepared from at least one polyisocyanate with at least one polyol; and
at least one catalyst system obtained from components consisting of one bismuth compound and one aromatic nitrogen compound, wherein the aromatic nitrogen compound is coordinatively bonded with bismuth, and the aromatic nitrogen compound has the formula A or B,
where:
R1, R2, R3, R4, R5 and R6 each independently of one another is H, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, tert-butyl, C 5 to C 12 alkyl, COOH, COOR′ or halogen,
R7 is a C 1 to C 8 alkyl, a hydroxyl group (OH), O—(CH 2 CH 2 O) x —R′ with the values for x of 1-6, or O—(CH 2 CH(CH 3 )O) x —R′ or a positional isomer thereof, with the values for x of 1-6,
R8 is alkylene or alkylene ether,
R′ is alkyl, and
R″ is alkyl or alkyl with heteroatoms.
2. The one-part polyurethane prepolymer composition of claim 1 , wherein the aromatic nitrogen compound is the aromatic nitrogen compound of formula B, and wherein R8 is a C 1 to C 8 alkylene, (CH 2 CH 2 O) y CH 2 CH 2 , (CH 2 CH(CH 3 )O) y CH 2 CH(CH 3 ) or a positional isomer thereof, with the values for y of 0-5.
3. The one-part polyurethane prepolymer composition of claim 1 , wherein, in the aromatic nitrogen compound of formula A or B, the substituents R1, R2, R3, R4, R5 and R6 each independently of one another is H or methyl.
4. The one-part polyurethane prepolymer composition of claim 1 , wherein the bismuth compound is a bismuth carboxylate Bi(OOC—R′″) 3 , where R′″ is a C 5 to C 17 alkyl radical.
5. The one-part polyurethane prepolymer composition of claim 1 , wherein in the catalyst system a molar ratio of (aromatic nitrogen compound multiplied by the denticity of the aromatic nitrogen compound) to bismuth is 0.2:1 to 12:1.
6. The one-part polyurethane prepolymer composition of claim 1 , wherein there is also at least one tin compound present.
7. The one-part polyurethane prepolymer composition of claim 1 , wherein the composition is moisture-curing.
8. A process for preparing the one-part polyurethane prepolymer composition of claim 1 , comprising a step of preparing the catalyst system by reacting a bismuth compound with at least one aromatic nitrogen compound.
9. An adhesive, sealant, coating or lining comprising the one-part polyurethane prepolymer composition of claim 1 .
10. A primer comprising the one-part polyurethane prepolymer composition of claim 1 .
11. A method of adhesively bonding, sealing or coating a surface, comprising contacting the surface with the one-part polyurethane prepolymer composition of claim 1 .
12. The method of claim 11 , wherein the surface is a paint.
13. The method of claim 11 , further comprising curing the contacted surface in air.
14. The method of claim 11 , further comprising contacting the surface with a water-containing component or an admixture thereof.
15. A catalyst for polyurethane compositions, wherein the catalyst is a coordination compound between bismuth and an aromatic nitrogen compound of the formula A or B,
where
R1, R2, R3, R4, R5 and R6 each independently of one another is H, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, tert-butyl, C 5 to C 12 alkyl, COOH, COOR′ or halogen,
R7 is a C 1 to C 8 alkyl, a hydroxyl group (OH), O—(CH 2 CH 2 O) x —R′ with the values for x of 1-6, or O—(CH 2 CH(CH 3 )O) x —R′ or a positional isomer thereof, with the values for x of 1-6,
R8 is alkylene or alkylene ether,
R′ is alkyl, and
R″ is alkyl or alkyl with heteroatoms.
16. A catalyst for polyurethane compositions, wherein the catalyst is a coordination compound between bismuth and 8-hydroxyquinoline or between bismuth and tetraethylene glycol bis(8-quinolyl) ether.
17. A process for preparing a polyurethane prepolymer, comprising catalyzing a reaction of at least one polyisocyanate with at least one polyol with a catalyst of claim 15 .
18. The one-part polyurethane prepolymer composition of claim 1 , wherein R7 is OH.
19. A one-part polyurethane prepolymer composition comprising, in a single part,
at least one polyurethane prepolymer having terminal isocyanate groups, prepared from at least one polyisocyanate with at least one polyol; and
a catalyst system consisting of a catalyst obtained from components consisting of one bismuth compound and one aromatic nitrogen compound, wherein the aromatic nitrogen compound has the formula A or B,
where:
R1, R2, R3, R4, R5 and R6 each independently of one another is H, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, tert-butyl, C 5 to C 12 alkyl, COOH, COOR′ or halogen,
R7 is a C 1 to C 8 alkyl, O—(CH 2 CH 2 O) x —R′ with the values for x of 1-6, or O—(CH 2 CH(CH 3 )O) x —R′ or a positional isomer thereof, with the values for x of 1-6,
R8 is alkylene or alkylene ether,
R′ is alkyl, and
R″ is alkyl or alkyl with heteroatoms.Cited by (0)
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